1-Hydroxy-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran-9-carboxylic acid → HCID 57264109, compound

HRID 1034372Notes

Reaction equation

HRID 1034372 reaction equation
[OH:1][C:2]1[C:11]2[C@@H:10]3[CH2:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][CH2:15][C@H:9]3[C:8]([CH3:20])([CH3:19])[O:7][C:6]=2[CH:5]=[C:4]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:3]=1.COC(C1C[C@@H]2C3C(O)=CC(CCCCC)=CC=3OC(C)(C)[C@H]2CC=1)=O>>[OH:1][C:2]1[C:11]2[C@H:10]3[CH2:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][CH2:15][C@@H:9]3[C:8]([CH3:19])([CH3:20])[O:7][C:6]=2[CH:5]=[C:4]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:3]=1

Participants

3

Reactant 2

HCID 1623891-Hydroxy-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran-9-carboxylic acidHCID 57202167HCID 57202167, compound

Product 1

HCID 57264109HCID 57264109, compound

Procedure

By the same procedure described before for preparing (XI) in Example 7, hydrolysis of the (6aS,10aS)-ester (XVII) (22 mg, 0.061 mmol) with argon sparged 2N NaOH (3 mL) in argon sparged methanol (4 mL) at room temperature for 18 h gave, after work-up, 22 mg of a gum. This was subjected to preparative TLC on silica, eluting with hexanes-CHCl3 -MeOH (7:2:1) to give, from the main band, 16 mg, 76%, of the (6aS,10aS)-acid (XVIII) as a glass, [α]D +310° (CHCl3), M+ 344.1983 (Calc 344.1988).

Workup

  1. customsparged 2N NaOH (3 mL) in argon
  2. customsparged methanol (4 mL) at room temperature for 18 h
  3. customgave
  4. washeluting with hexanes-CHCl3 -MeOH (7:2:1)

Sources & evidence

ORD record
ord-b620d0903e9a4ef29e22966d16ee9e9a
Source dataset
uspto-grants-1994_05
Patent number
US05315015

Reaction notes

Loading…